Incessant tinkerer since the 70’s. Staunch privacy advocate. SelfHoster. Musician of mediocre talent. https://soundcloud.com/hood-poet-608190196

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Joined 11 months ago
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Cake day: March 24th, 2025

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  • when using Tailscale you can not use another WireGuard based VPN according to their FAQs.

    Anecdotally, if I turn off the Advanced killswitch and The VPN killswitch of my main VPN, I can actually bring up Tailscale. But you are right, it does add complexity. Basically I use Tailscale on the server and pFsense firewall as an overlay VPN. It’s also handy if you lock yourself out of the server. A ‘backdoor’ of sorts.


  • As you already have a VPN active at all times (at least it sounds like that), a VPN home seems out of the picture.

    Expand on that, if you would. I run local VPN and everything else through Cloudflare. In fact the VPN DNS is Cloudflare as well as the stand alone pFsense firewall. Perhaps I am misunderstanding, which is likely since I’m all drugged up trying to pass a kidney stone.


  • I’m trying to get the best of 2 worlds: using the VPN to hide my IP from services that i visit and my ISP, and a secure connection to my home server.

    How about Cloudflare Tunnels/Zero Trust? The caveat being that you have to own a domain that you can change the nameservers to the ones Cloudflare assigns you. You can purchase a domain from Cloudflare, but I think a lot of people get one from NamesCheap or PorkBun. I purchased on for less than $5 USD. With Cloudflare Tunnels/Zero Trust, you don’t have to open ports, fiddle with NAT, or any of that. You install it on your server and it punches a hole in to allow communication.

    Some people like Cloudflare, some people don’t. Personally, I’ve never had any issues except for a very brief downtime a while back.



  • Would it make you feel better if you paid Tailscale for one of their plans? It’s not like they are just giving away their whole enterprise. It’s fairly trivial for them to give free services, kind of like Cloudflare, Oracle, et al. Reading a bit reveals:

    • Tailscale’s estimated annual revenue is currently $45.2M per year.
    • Tailscale’s estimated revenue per employee is $230,489
    • Tailscale’s total funding is $277M.
    • Tailscale’s current valuation is $1.5B. (April 2025)
    • Tailscale has 196 Employees.
    • Tailscale grew their employee count by 23% last year.

    That seems pretty profitable. Enshitification happens. It’s been going on since I was born. If it’s free on the internet, and later it becomes a paid service, then I just find something else that fits. Or pony up the cheapest plan they have, which currently is their Personal Plus @ $5 USD per month. I don’t mind paying for a good service and $5 USD is burger from McDonalds. Extremely well under what most people put into a hobby. Will prices increase? Maybe…everything goes up. Rarely do services and utilities go down in price. When the price points are no longer justifiable, again, I look for something else that fits.